4-(2-Aminoanilino)pyridine → (E)-2-[2-(3-Furyl)ethenyl]-1-(4-pyridyl)-1H-benzimidazole

HRID 50908Notes

Reaction equation

HRID 50908 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])=[CH:3][CH:2]=1.[O:15]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22](Cl)=O)=[CH:16]1.N1C=CC(N2C3C=CC=CC=3N=C2/C=C/C2C=CC=CC=2)=CC=1>>[O:15]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]2[N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:16]1

Participants

4

Reactant 3

HCID 2911324-(2-Aminoanilino)pyridineHCID 9948158(E)-1-(4-Pyridyl)-2-styryl-1H-benzimidazoleHCID 22736687(E)-3-(Furan-3-yl)acryloyl chloride

Product 1

HCID 22736738(E)-2-[2-(3-Furyl)ethenyl]-1-(4-pyridyl)-1H-benzimidazole

Procedure

The titled compound was prepared from N-(4-pyridyl)-o-phenylenediamine and (E)-3-(3-furyl)acryloyl chloride according to the preparation of (E)-1-(4-pyridyl)-2-styryl-1H-benzimidazole (Example 3). MW: 287.32; mp: 171.5-172.5° C.; 1H-NMR (DMSO) δ: 8.88 (2H, dd, J=4.6, 1.7 Hz), 8.07 (1H, br.s), 7.81 (1H, d, J=15.8 Hz), 7.74-7.65 (4H, m), 7.35-7.25 (3H, m), 6.89 (1H, br.s), 6.73 (1H, d, J=15.8 Hz).

Sources & evidence

ORD record
ord-f2a3f464c92a413f868c331fbf2f5be5
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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